Tetrahydrofuran → HCID 23364263, compound

HRID 1081510Notes

Reaction equation

HRID 1081510 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[CH:21]=[CH:20][C:9]2[NH:10][C:11](=[O:19])[N:12]([CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[C:8]=2[CH:7]=1)[CH3:4].C1COCC1.[CH3:27][O:28][C:29]([C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[C:33]([O:41][CH3:42])[CH:32]=1)=[O:30]>O.CN(C=O)C>[CH2:3]([O:5][C:6]1[CH:21]=[CH:20][C:9]2[N:10]([S:37]([C:34]3[CH:35]=[CH:36][C:31]([C:29]([O:28][CH3:27])=[O:30])=[CH:32][C:33]=3[O:41][CH3:42])(=[O:39])=[O:38])[C:11](=[O:19])[N:12]([CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[C:8]=2[CH:7]=1)[CH3:4]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 22922597HCID 22922597, compoundHCID 23364278162141-56-2

Product 1

HCID 23364263HCID 23364263, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.18 g of sodium hydride as a 60% dispersion in oil is added in portions to a mixture of 1 g of 5- ethoxy-1,3-dihydro-3-(tetrahydropyran-4-yl)-2H-benzimidazol-2-one, 30 ml of THF and 20 ml of DMF and the mixture is stirred for 30 minutes at RT. 1.2 g of 4- methoxycarbonyl-2-methoxybenzenesulfonyl chloride are then added and the mixture is stirred for 3 hours at RT. The reaction mixture is poured into 200 ml of water and the precipitate formed is filtered off and washed with iso ether to give 1.13 g of the expected product after drying. M.p.=165° C.

Workup

  1. stirringthe mixture is stirred for 3 hours at RT
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. washwashed with iso ether

Sources & evidence

ORD record
ord-abbe2e8dac95407490eb9b93c3dd6b85
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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